Using data from the Future of Families and Child Wellbeing Study, we estimate associations of paternal incarceration with three measures of teens’ attitudes and expectations: (1) optimism about the future, (2) perceived importance of college graduation, and (3) perceived likelihood of college graduation. Results suggest that whereas optimism toward the future and the importance of college are resilient in the face of paternal incarceration, teens’ expectations of actual college completion are reduced, particularly for Black youth. An examination of micro-, meso-, and macro-level mechanisms suggests that early consequences of paternal incarceration influence perceptions of future educational trajectories. Our findings point to the complexity of contemporary teens’ college-related attitudes in the wake of the prison boom. Signs of optimism surfaced, yet obstacles associated with paternal incarceration represent a type of racialized constraint. An updating of the educational expectations literature is needed to account for the racialized nature of the era of mass incarceration in the United States.